3-Fluoroacetophenone → HCID 22379891, compound

HRID 895581Notes

Reaction equation

HRID 895581 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[Li+].CC([N-]C(C)C)C.[Br:19][C:20]1[CH:32]=[CH:31][C:23]2[N:24]([CH2:29][CH3:30])[C:25]([CH2:27]Cl)=[N:26][C:22]=2[CH:21]=1>C1COCC1>[Br:19][C:20]1[CH:32]=[CH:31][C:23]2[N:24]([CH2:29][CH3:30])[C:25]([CH2:27][CH2:9][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[O:10])=[N:26][C:22]=2[CH:21]=1

Participants

5

Reactant 3

HCID 99673-FluoroacetophenoneHCID 2724682Lithium diisopropylamideHCID 22379875HCID 22379875, compound

Product 1

HCID 22379891HCID 22379891, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(3-fluoro-phenyl)-ethanone (0.55 g, 4.0 mmol) in THF (30 mL) at −78° C. under N2 is added LDA (2M in hexanes, 2.0 mL, 4.0 mmol). After 10 minutes, 5-bromo-2-chloromethyl-1-ethyl-1H-benzoimidazole (1 g, 3.65 mmol) in THF (5 mL) is added. The mixture is stirred at this temperature for an additional 1 hour and is gradually warmed to room temperature. The reaction is then quenched with saturated NH4Cl. The mixture is extracted with ethyl acetate (3×50 mL). Upon drying, the organic solvent is removed to give 3-(5-Bromo-1-ethyl-1H-benzoimidazol-2-yl)-1-(3-fluoro-phenyl)-propan-1-one as a yellow oil.

Workup

  1. customThe reaction is then quenched with saturated NH4Cl
  2. extractionThe mixture is extracted with ethyl acetate (3×50 mL)
  3. customUpon drying
  4. customthe organic solvent is removed

Sources & evidence

ORD record
ord-aea7e87631904f46a3877f057e83fb46
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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